


50 Shades of Dean

by jeffwingersimp



Category: Community (TV)
Genre: Greendale, M/M, blowjob
Language: English
Status: In-Progress
Published: 2020-07-24
Updated: 2020-08-05
Packaged: 2021-03-04 22:34:56
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,910
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25493959
Author URL: https://archiveofourown.org/users/jeffwingersimp/pseuds/jeffwingersimp
Summary: The Dean finds out the Jeff has been taking fake classes. Jeff will pass, only if he agrees to a date.
Relationships: Dean Craig Pelton/Jeff Winger
Kudos: 6





	1. First Date

**Author's Note:**

> This is my first fanfiction ever! I hope that you enjoy reading it.

One day, Craig and Jeff were hanging out after school in Craig's office. Dean Craig had realized that Jeff picked a fake class, and he was confronting him about it. Jeff sat down and looked around the office. “Why am I here? I was going to go on a date with a nice catch tonight.” he looked disappointed and annoyed. He glared at Craig as he watched him sit down.   
“I have figured out you have picked a fake class, I knew you were a slacker, but I didn't think that you slacked off that much! We will have to take off credits for your class, unless you can do me a favor!” he winked and stared at Jeff, hoping that the man he thought was the hottest would accept. He really wanted the two of them to do something nice and fun together, maybe something spicy.  
“Ugh, I can probably guess what you want, I don’t want to do it,” he groaned, looking at Craig, lots of ideas popping in his head of what the Dean might do to him, “You are gonna make me do some weird sex thing or something.”  
“N-No, I totally wasn’t… But if you don't accept my offer, you will have to repeat a whole year of college, so you better accept,” Craig smirked, aiming a teasing look towards Jeff.  
“Fine, I don’t wanna spend another year in this place anyways.” He glanced around the room, catching sight of all the strange things in the office, pictures of dalmations and Jeff were all over the walls, and there were some questionable videos playing muted on the Dean’s laptop. Jeff shuddered at the thought of what Craig could do to him.  
“Great! I wanna go on a date with you, and maybe… Something else after,” Craig exclaimed, a beaming smile on his face, “Lets go get ice cream!” he stood up, chuckled lightly, and took Jeff’s hand. He blushed and stared into Jeff’s beautiful eyes.  
Jeff rolled his eyes and pulled his hand away. “Let’s just get this over with.” He walked out of the room with Craig, blushing slightly. Jeff had always secretly liked Craig, although he kept it a closely guarded secret, only Abed knew. Jeff stepped outside and looked around in the fresh air, smiling because it was a nice day. He took Craig’s hand and looked at him shyly. “I’ll drive us there,” he said, walking towards his Lexus. He got into the car, Dean following, and he put his key into the ignition.  
“This is gonna be great,” Craig said, resting his head on Jeff’s shoulder. “Which ice cream place should we go to?”  
“I think we should go to the one 10 minutes away,” he said, looking into Craig’s eyes. They were so beautiful, so deep. He then realized he had to drive, so he pushed down on the gas pedal and pulled out of his parking spot. As he drove, Jeff thought about the events of today. He wondered who snitched on him for having a fake class, and how he was so lucky to spend time with the man he secretly loved. He lifted one of his hands off of the steering wheel and grabbed Craig’s hand. He blushed and kept on driving. Craig almost fainted when Jeff had grabbed his hand. He wasn’t expecting Jeff to actually willingly touch him. Soon they made it to the ice cream place  
“Yay! We’re here! What kind of ice cream do you want?” Craig asked, looking at Jeff with a sly smile on his face. “I like mint chocolate chip ice cream.”  
“Hmmm…. You can pick for me, I trust you,” Jeff smiled, his gaze darting over to the many flavors of ice cream.   
“I think you would like cookie dough ice cream,” Craig said, smiling softly, “It is very yummy.” Craig held Jeff’s hand as they walked together to the ice cream place.  
“Can we get 1 scoop of cookie dough and one scoop of mint chocolate chip?” Jeff asked, looking at the man at the counter. Craig proudly grinned, standing next to Jeff happily. They got their ice cream, then they sat in Jeff’s car, eating and talking.  
“This is the best date ever, dream come true!” Craig said, happily licking his ice cream. “I never thought I would get to have a day like this!” He grinned and hugged Jeff.   
“Heh, this isn’t as bad as i thought, this date is probably better than whatever i would've gotten with that girl i was gonna go out with,” Jeff stated, looking at Craig. “I like you, I was just too arrogant to mention it before. What should we do now, I’m almost done with my ice cream!”  
“I want to go to your place,” Craig said, finishing up his ice cream. He softly touched Jeff’s chest and sighed softly. “You have been so nice to me today, do you really like me like that?” Craig was a bit worried that Jeff was just playing with him, as he had been rejected many times in the past by Jeff.   
“Maybe I do, maybe I don’t, you can ask Abed later,” Jeff said, looking at the ground. He seemed pretty nervous. “Let’s just get to my house…” He started up his car and drove off. He felt hurt that Craig didn’t trust him. Jeff knew that he was never a trustworthy person, but for some reason it hurt this time, not being trusted. He sighed and took his eyes off the road for a minute to look at Craig. He hoped that he could get Craig to trust him so they would be able to spend more time together. He looked back at the road and continued driving. The traffic was pretty bad and he groaned. “It might be awhile,” he stated, looking back at Craig.  
Craig nervously looked at Jeff. “I hope it doesn’t take too long, I want to spend as much time as I can with you.” He smiled softly and held one of Jeff’s hands, his smile got wider as he felt the warmth of Jeff’s hand. He thought about what the future could be if he stayed with Jeff forever, he sighed and smiled. He would cherish these moments, he didn't know if Jeff actually liked him or not.  
After a half an hour of them talking and driving, they made it to Jeff’s apartment complex. Jeff parked in the parking lot and took the keys out of the ignition. He grabbed his stuff and Craig’s stuff as Craig stood next to the car waiting for Jeff. “I should help you carry some of that in!” Craig exclaimed, grabbing half of the stuff. He blushed and walked next to Jeff as they went into the building. The pair walked toward Jeff’s apartment and arrived there shortly. Jeff turned the key into the lock, and opened the door.   
“Well, we are home now,” Jeff said, putting down his stuff and walking towards the fridge. He took out some scotch from the fridge and brought it to the couch. He set it on the table next to the couch and reclined back. He motioned to his lap, inviting Craig to sit on his lap.  
“O-Oh, I can sit there!” Craig stammered, walking up to Jeff’s lap. He sat there, sheepishly grinning. “Thank you Jeff,” He said, melting into Jeff’s warm embrace.   
Jeff wrapped his hands around Craig, smirking, “What are we gonna do tonight, baby~” Jeff said, softly chuckling. He knew the smaller man would melt at this very sentence, and he was determined to dominate Craig.   
“O-Oh, you can choose, D-Daddy,” Craig said, looking up at Jeff with a glint of fear in his eyes. He watched as Jeff took his shirt off, his rock-hard abs shining in the light. Craig drooled at the sight of them and reached out to touch them. Jeff grabbed Craig’s hand.  
“Not yet, honey, you gotta wait to touch those,” Jeff said, smirking and looking down into Craig’s eyes. He removed his pants, then he let Craig pull down his underwear. Jeff’s cock was pretty large, a great size in Craig’s opinion. He looked up at Jeff, silently asking permission to give Jeff a blowjob. “Sure, baby, you can pleasure me~” Jeff said, letting Craig take his dick. The dean profusely sucked Jeff’s fallace, pleasuring him. Jeff moaned softly, “Good job, babyboy~” he smirked and pulled off Craig’s pants and underpants. He grabbed Craig’s dick, and started tugging on it softly, giving a handjob. Craig moaned softly as he kept on sucking Jeff’s penis. Suddenly, Jeff gasped softly and cummed in Craig’s mouth. The submissive swallowed and pulled the long dick out of his mouth. He buckled back in pleasure as Jeff continued giving him that handjob. Soon, Craig cummed, cum spraying everywhere, hitting the sides of the couch and table. He panted softly and collapsed into Jeff’s arms.  
“Was that good, hun?” Jeff asked, softly holding the exhausted dean. He smiled softly as he saw that the dean was curled up in his arms. “Do you need anything?”  
“I liked that a lot, and can i have some water please…” Craig said snuggling close to Jeff. “Can you carry me when we get water too, please,” he said, whimpering softly.  
“Sure, babyboy,” Jeff said, standing up, the dean resting in his arms. He walked over to the kitchen and grabbed a water bottle out of the fridge, opened it, and handed it to Craig.  
“Thank you, Daddy,” Craig said, drinking the cold, refreshing water. He felt very comfortable and safe, nestled in Jeff’s arms with the water bottle in his hands. Jeff grinned and took them to the couch. He cleaned up everything, then looked at Craig.   
“Do you want to go to my bed now?” he asked, looking down at Craig. “I have a lot of blankets there, we can cuddle.” Craig nodded, and Jeff took him to the bed. He gently set down Craig, and laid down besides him. “You are so cute,” Jeff mumbled, looking over at Craig. He snuggled close to the one he desired and snuggled close. They both closed their eyes, and they slowly drifted off to sleep, holding each other.


	2. The Mall

Craig woke up late in the morning. He yawned and stretched, looking outside at the sunshine, and he heard birds singing.Then, he heard a soft snoring noise and looked next to him. He spotted Jeff next to him, still sleeping. He was confused for a second, but then the events from last night flooded back into his memory. Craig blushed and poked at Jeff’s face.  
Jeff groaned and sat up. He looked at Craig, remembering it all. “Oh God this actually happened,” Jeff said, looking like he was going to have an anxiety attack. He looked at Craig, fear in his eyes, “Did I go too far last night? I’m not even sure if this is real,” Jeff said, frowning. He looked at Craig, anxiety showing through his eyes.  
“It's going to be ok, Jeffery, you didn’t go too far yesterday, it was quite nice,” Craig said, snuggling closely to Jeff to try to calm him down. “We can work through this together, it will be ok.” He glanced across Jeff’s apartment, noticing a large mess on the floor. “I can take care of that, you should rest, sweetheart,” Craig stated, pointing at the sea of clothes on the floor. He gave a little peck on the cheek to Jeff, then he worked on cleaning up the mess from last night. He grinned as he picked up Jeff’s shirt, taking a glance at the light blue fabric. “I really like how this shirt looks on you, you should wear it more often!” He set down the shirt gently on the couch, then picked up the rest of the clothes. After the mess was taken care of, Craig put on Jeff’s blue shirt and chuckled. “Do I look good?” He asked, looking over at his man who was laying on the bed.  
“I think you look very adorable!” Jeff said, “You might even look even better than I do when I wear that shirt!” He opened his arms, inviting the dean to come over to cuddle. Craig ran over and jumped onto the bed, leaping into Jeff’s arms. Jeff giggled and wrapped his arms tight around Craig and flopped down into the bed. The pair snuggled in bed happily, enjoying each other’s warmth. Jeff gave Craig a light kiss on the head, and sighed happily. This day was going very well so far. “What should we do today, honey. Do you want to go to the mall?” Jeff asked, looking over at his beloved.  
“I really think that's a great idea! We could both get some new clothes!” Craig exclaimed, sitting up. He grinned and took Jeff’s hand, “Let’s go!” he bounced off of the bed and scrambled across the room to get some more clothes on. Jeff smiled softly, and calmly got off of the bed, selecting some new clothes from his closet.   
“Are you ready?” Jeff asked, putting on his clothes. He walked over to Craig, taking his hand. Craig softly nodded and opened the door. The pair walked out to Jeff’s car and got in. “Today is gonna be nice,” Jeff said, smiling. He turned the keys into the ignition. “You can pick what music we listen to.”  
Craig grinned and turned it to a station with pop music. He sang along to the songs. Jeff listened, a small smile on his face. Craig’s voice was beautiful, loudly ringing through the car. Jeff shyly began to sing, glancing over at Craig for a second, taking in his beautiful smile. He couldn’t believe that he hadn’t seen the dean in this way sooner.  
Jeff looked over at the road, concentrating on driving. His thoughts kept wandering to last night, and what they did. He liked it a lot, and he was scared to admit it. Jeff thought that he was straight, but he had been questioning his sexuality ever since he met the dean. He was very anxious about entering a relationship, since he had commitment issues in the past. At the same time, he did not want to break Craig’s heart, he really liked him. Jeff dwelled on his thoughts until they arrived at the mall.  
“Oooo, we’re here! This mall is undeanlievably large!” he exclaimed, giggling at his own pun. He looked at Jeff and touched his abs softly. Jeff smiled nervously and didn’t push him away. Craig looked into Jeff’s eyes and saw the anxiety. Craig’s eyes softened, and he hugged Jeff. “Everything is gonna be ok, I know all of this is a lot, and i’m sorry if it was all too much for you,” Craig said, letting go of Jeff, “If you want this to end now, I’d understand.” The dean looked sad, but he would always do what made Jeffrey comfortable, no matter how much it went against his own feelings.  
“No, I really like you, I think I might be able to try a relationship again,” Jeff said, nervous smile still on his face, “You are a great man, and I think it will be worth it to try with you.” Jeff gazed over at the mall, seeing the Gap store. “Let’s go shopping, this reminds me of the time you made me go on a date with you,” Jeff said, chuckling.  
Craig blushed, looking down at the ground, “I am truly sorry about that, I just really liked you and-” he wasn't able to finish his sentence, Jeff pulled him into a passionate kiss. Jeff opened up his mouth so Craig could slide in his tongue, and Craig copied. The pair made out for at least a minute, then Jeff pulled away. Craig blushed and looked at Jeff. “I-I liked that a lot,” he stated, giggling softly. He grabbed Jeff’s hand and smiled.  
The pair walked into the mall, making a beeline for the Gap store. “What section should we look at first?” Jeff asked, stopping right at the inside of the store. He looked around and smiled. “Maybe we should look at watches first."  
Craig nodded, "Maybe you will find something nice," he said, "a gold watch would look very good on you, I bet we will find the perfect one!" On the way to the watches, they noticed the other jewelry in the section. Craig picked up a really pretty red ruby necklace and stared at it in awe. "Oh my gosh! This would be so pretty with my red dress!" He gasped and checked the price. "Oh gosh, it's $150, maybe I don't need it…" He was about to set it down before Jeff spoke up.  
"No, we can split the cost, I bet it would look beautiful on you," Jeff said, grinning. He took a look at the glittering necklace and imagined the dean wearing. Just the thought of that was good enough to buy it.  
“B-But its so expensive! I don’t want you to waste your money!” Craig stuttered, looking down at the ground. He really wanted the necklace, but he didn’t want to have Jeff pay for it. He still couldn’t shake the feeling that Jeff was just faking all of this, and he was going to return to his normal state of rejecting the dean when they went back to school.   
Jeff interrupted his thoughts, “Come on, honey, let's look for my watch now.” He walked next to Craig, and they reached a display case full of watches. There were so many of them, and Jeff’s eyes glittered. After a bit of gazing at the shimmering, expensive watches, Jeff’s eyes set on one watch. It was a gold and light blue Rolex, the band was shiny, and the watch had small numbers etched in gold. He gasped. “That watch is perfect…” he said, smiling. Jeff got a worker to take it out of the case, and he tried it on. The watch fit perfect, it wrapped around his arm nicely. “I think I am going to buy this,” he said, looking at Craig  
“It looks so good on you! I love it,” Craig said, smiling supportively at Jeff. He was excited that Jeff had found the perfect watch. Craig thought that Jeff was really adorable getting excited over the watch. Craig clutched his necklace gently, and looked at it. He was so happy that they had both found something, and not too much time had passed by. So far this date with Jeffrey had been really good, Craig hoped that it would get even better.  
Jeff smiled, and hugged Craig, "This is so great, I haven't had a better date than this ever!" He smiled, and kissed Craig’s nose. “What do you want to look at next in the store?” Jeff asked, softly patting Craig’s head.  
“C-Can we look at the dresses? I kind of want a new costume,” he stated, blushing softly. He was scared that Jeff was going to make fun of him, and he really didn’t want to be humiliated at the mall.  
Jeff smirked, “I bet you will look super cute in a dress I pick out for you” He took Craig’s hand and led him to the women’s section. Craig looked around at all of the clothes in awe, seeing so many cute options. Jeff looked through a rack, humming softly. He wanted to find a nice, tight dress for Craig. He imagined Craig’s fine ass being shown off with a nice dress. He sighed softly and looked at Craig. “What is your favorite color?” he asked, staring at the various colors of dresses. He really wanted the dean to have the most perfect dress, and most importantly, he wanted Craig to feel confident in his clothes.  
“I like red dresses,” Craig said, blushing softly. He had never been dress shopping with anyone, and he was feeling happy that he finally got to do that. He spotted a red dress, and felt it. It was velvety, and it felt very luxurious. Craig found his size, and took it off of the rack. “I think I am going to try this on, it looks really nice,” Craig giggled, and held the dress up against his body. “Maybe I should also try one size up just in case.” He grabbed another dress, and he walked to the dressing room, Jeff following closely behind.  
Jeff loved hearing the glee in Craig’s voice, and he enjoyed the smile on his beautiful face. Jeff didn’t know how he had deserved this beautiful man, but he was glad to watch him enjoying himself. Jeff waited as Craig put on the dress in the dressing room, and gasped when Craig stepped out. Craig looked stunning, the dress clung smoothly and tightly around him, accenting his ass and small curves.   
“How do I look?” Craig asked, shyly smiling. Craig giggled softly and smiled.  
“You look amazing,” Jeff said, his eyes softening. He grinned, “I feel like this is the perfect dress for you, I love it.”  
“Yeah, I agree, I like how it looks on me. I’m going to get changed back, ok?” Craig asked. Jeff nodded, and Craig went back into the changing room. Craig walked back out, wearing Jeff’s light blue shirt and Craig’s sweatpants again. Craig held out his hand, and Jeff took it.  
They kept shopping at the mall all day. After a long day at the mall, the two were laughing and chatting as they walked back to Jeff’s car. They were each carrying a lot of bags from various stores, and they were very happy. They put the bags in the back seat, and they got into the car. Interlocking their fingers, the pair were getting ready to leave. Jeff started the car with his other hand, and the car pulled out of the parking spot. They chatted the whole way home, the streetlamps shining and illuminating their faces in the night.


	3. Shower Time

**Summary for the Chapter:**

> Showering together

Jeff and Craig arrived home after about 20 mins of driving. They got out of the car and got all of their bags out of the car. Jeff smiled down at Craig. “We got so much!” He said, chuckling softly. He smiled and held out one of his hands.  
Craig grabbed the hand and smiled. The two of them walked into their apartment building. “Can we go to my place tonight?” Craig said, smiling softly. He wanted to show Jeff his apartment.  
“Sure, I wonder what your place looks like!” Jeff said, opening the front door of the apartment complex. They walked up the stairs, and reached their floor. Jeff stopped in front of Craig’s door.  
Craig grabbed his key out of his pocket and fumbled with the lock. After a few seconds, he unlocked the door, and he opened it slowly. The door creaked, and they stepped inside. Craig’s apartment was a bit messy, costumes and makeup in one corner of the main room. He had pictures of dalmations and Jeff all over the wall. Jeff looked around, chuckling. “Wow, there's pictures of me, I knew it,” He said, looking at Craig  
“Oops, I forgot to take those down,” Craig said, looking around nervously. He never thought that Jeff would ever be in his apartment, but today was the day for that. He was nervous that Jeff was going to think that his place was disheveled and random. He looked over at Jeff with a shy smile on his face, and anxiety in his eyes.  
“It’s ok, I think it's pretty cute that you have pictures of me everywhere,” Jeff said, planting a soft kiss on Craig’s head. He smiled softly, and sat on the couch, motioning the dean to sit next to him.   
Craig settled down next to Jeff, snuggling into him. He turned on the tv, and it was on some random late night channel. He yawned and closed his eyes.  
Jeff looked at him and grinned. He thought Craig was so cute right now. He softly patted the smaller man’s head, and looked towards the tv. Craig slowly fell asleep, and Jeff didn’t move, not wanting to wake the softly snoring man. He watched the tv, engaged in the stuff on the screen. He let his thoughts wander. He felt so lucky that he got to sit on the couch with Craig, and he was happy that he could be nice and comfortable watching tv.Jeff closed his eyes and dozed off, feeling warm and safe.  
At about 3 AM, Jeff woke up, hearing whimpering from beside him. He looked and his eyes softened. Craig was clearly having a nightmare. Jeff gently rubbed Craig’s back and whispered a few reassuring phrases, gently speaking, “It’s just a dream, you’ll be ok.” Jeff continued speaking, starting to tell Craig about how he knew he loved him, even though Craig was still asleep. Craig stopped whimpering after a bit, and Jeff smiled. He held Craig close, and soon fell asleep again.  
Craig woke up at 9:30 AM, he looked, and saw that he was still nestled in Jeff’s arms. He moved around a bit to get comfortable, and he saw Jeff wake up. “Good morning!” Craig said, “What should we do, it’s still the weekend!” Craig giggled and looked up at Jeff.  
“I’m going to take a shower, you can make breakfast if you want!” Jeff said, kissing Craig’s nose and picking him up, setting the smaller man next to him. Jeff stood up and smiled. “I’ll only be showering for a bit, unless you want to shower with me?” He stated, winking at Craig.  
Craig blushed a bright red. He wasn’t expecting to hear that, he thought Jeffery would just shower alone. Craig took Jeff’s hand and stood up. “I’d love to!” He said, pulling Jeff towards the bathroom. He thought that this would be really fun, and he wanted to do it.  
They reached Craig’s bathroom and opened the door. It was very clean and tidy in there, compared to the rest of the house. Jeff smiled and let go of Craig’s hand. “Is it ok if I get some stuff from my apartment? I need my special shampoo.” Craig nodded, and Jeff walked out. Craig tidied up the bathroom some more and hummed softly. He made sure that the shower was pristine clean, not wanting Jeff to see any dirt or grime. Soon after he was finished Jeff returned, carrying some body wash, cologne, conditioner and his shampoo. “Sorry, that took longer than expected, I nearly forgot the code to my safe!”   
“It’s fine, I had time to tidy up the place even more, I wanted it to look just perfect for you!” Craig exclaimed, beaming. He opened up the shower curtain, and the tub and shower almost sparkled. Craig looked proud of the cleaning he had done, and Jeff smiled.  
“Great job, honey, you did amazing!” Jeff chuckled and looked at Craig. He took off his shirt, and smirked. “Let’s do this.”  
The pair removed all of their clothes, and made out furiously. Jeff stuck his tongue into Craig’s mouth, and Craig mirrored, moving his tongue around passionately. They kept at it for about a minute. They pulled away, looking at each other. "I think we should get in the shower now," Jeff said, laughing softly. He turned the shower on, and felt the water. It was pretty warm, so he stepped in.  
Craig stepped in after him, shivering slightly. He stared at Jeff, taking in his entire body. His chiseled abs, his beautiful face. Craig smiled softly, and grabbed some body wash. He started cleaning up his body, looking at Jeff who was rubbing some shampoo into his hair. "You're so hot…" Craig murmured, not realizing he was saying it out loud.  
"You are too," Jeff said, booping Craig's nose. Craig looked a bit startled, but he blushed softly and giggled after a moment. Jeff wrapped his arms around Craig, taking in the scent of his freshly washed body. After a bit, he let go of Craig. Jeff smiled and reached for the conditioner, working it into his hair, and rinsing it out carefully.   
Craig watched Jeff, and smiled softly. He liked how careful Jeff was when he was lathering up the conditioner in his hair. Craig knew that Jeff liked to look perfect, and his hair had to look perfect too. Jeff finished off by cleaning himself off with body wash, than he turned off the shower.  
The pair stepped out, Jeff grabbing two towels. He wrapped Craig up in a towel and smiled softly. Jeff kissed Craig's cheek, then wrapped a towel around his own body.  
After a bit of scrubbing with the towels, they were both nice and dry. Craig took Jeff's hand and they walked over to Craig's wardrobe. Jeff handed Craig one of his shirts, and he smirked. "You look cute when you wear my shirts," he stated.  
Craig blushed and took the shirt, "Thank you Jeffrey." He put on the shirt, selected a nice pair of underpants and a pair sweatpants to go with it. He sat down on his bed as Jeff put on his own clothes.  
Jeff joined him on the bed, putting his hand on top of Craig's. "That was really nice," he said happily, letting Craig lean against him. Jeff felt happy and content, and he loved spending time with the dean.


End file.
